O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Base Information

Chemical Name:O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate
CAS No.:503157-84-4
Molecular Formula:C₃₄H₄₉N₆O₁₁PS
Molecular Weight:780.836
Hs Code.:

Synonyms:O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

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Chemical Property of O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

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Technology Process of O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

There total 5 articles about O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (S)-4-(4-{[(2S,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphanyloxy}-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 503157-84-4
O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: With tert.-butylhydroperoxide; In toluene; acetonitrile; for 1h;
DOI:10.1021/jm021016y

Reference yield:

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 503157-84-4
O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / NaBH₄; LiCl / tetrahydrofuran / 72 h / Heating

2: 78 percent / p-toluenesulfonic acid / acetone / 4 h / Heating

3: 78 percent / 3 Angstroem molecular sieves; 1H-tetrazole; NH(iPr)2 / acetonitrile / 2 h / 20 °C

4: 3 Angstroem molecular sieves; 1H-tetrazole / acetonitrile / 1 h

5: tBuOOH / toluene; acetonitrile / 1 h

With 1H-tetrazole; tert.-butylhydroperoxide; sodium tetrahydroborate; 3 A molecular sieve; toluene-4-sulfonic acid; diisopropylamine; lithium chloride; In tetrahydrofuran; acetone; toluene; acetonitrile;
DOI:10.1021/jm021016y

Reference yield:

: 83345-46-4,282100-80-5
N-(tert-butyloxycarbonyl)-L-tyrosinol

: 503157-84-4
O-[N-Boc-2,2'-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / p-toluenesulfonic acid / acetone / 4 h / Heating

2: 78 percent / 3 Angstroem molecular sieves; 1H-tetrazole; NH(iPr)2 / acetonitrile / 2 h / 20 °C

3: 3 Angstroem molecular sieves; 1H-tetrazole / acetonitrile / 1 h

4: tBuOOH / toluene; acetonitrile / 1 h

With 1H-tetrazole; tert.-butylhydroperoxide; 3 A molecular sieve; toluene-4-sulfonic acid; diisopropylamine; In acetone; toluene; acetonitrile;
DOI:10.1021/jm021016y